Methanol → HCID 59818345, compound

An 8.2 g quantity of a mixture of 4′-fluoro-5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl)methanol 16b and 4′-fluoro-5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-carbaldehyde 56 [obtained, as a mixture, from a Suzuki coupling by methods described in WO2007/005572] was dissolved along with sulfamic acid (3.3 g) in a mixture of THF (50 mL) and water (50 mL). The solution was cooled in an ice bath. A solution of 80% NaClO2 (2.6 g) in water (50 mL) was added dropwise from an addition funnel. When addition was complete, the mixture was stirred at <8° C. for 1.5 hr. The mixture was quenched by addition of water and extracted with EtOAc. The organic phase was concentrated under reduced pressure to a volume of 50 mL and extracted with 2N KOH (20 mL×2). The organic phase was reserved. The aqueous solution was acidified to pH 2, and the solid filtered, to yield 300-400 mg of product 57 as a first crop. The reserved organic solution was concentrated under reduced pressure and the resulting crude product purified by chromatography on silica gel to give a total of 1.4-1.5 g of 57.

1. customobtained, as a mixture, from a Suzuki coupling by methods
2. temperatureThe solution was cooled in an ice bath
3. additionWhen addition
4. customThe mixture was quenched by addition of water
5. extractionextracted with EtOAc
6. concentrationThe organic phase was concentrated under reduced pressure to a volume of 50 mL
7. extractionextracted with 2N KOH (20 mL×2)
8. filtrationthe solid filtered

ORD record

ord-12b875263df44b8ea2c0e801dbc15dbb

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759383B2